FI85373C - Analogiförfarande för framställning av terapeutiskt användbara pyridaz inaminderivat - Google Patents

Analogiförfarande för framställning av terapeutiskt användbara pyridaz inaminderivat Download PDF

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FI85373C
FI85373C FI851177A FI851177A FI85373C FI 85373 C FI85373 C FI 85373C FI 851177 A FI851177 A FI 851177A FI 851177 A FI851177 A FI 851177A FI 85373 C FI85373 C FI 85373C
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formula
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aryl
lower alkyl
hydrogen
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FI851177L (fi
FI851177A0 (fi
FI85373B (fi
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Raymond Antoine Stokbroekx
Der Aa Marcel Jozef Maria Van
Joannes Josephus Maria Willems
Marcel Gerebernus Maria Luyckx
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Janssen Pharmaceutica Nv
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/20—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/22—Nitrogen and oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Communicable Diseases (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Virology (AREA)
  • Oncology (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicinal Preparation (AREA)

Claims (8)

1. Analogiförfarande för framställning av terapeu-tiskt användbara pyridazinaminderivat med formeln I 5 N—N R1—(I) R2 R3 10 och/eller farmaceutiskt godtagbara syraadditionssalter och/eller möjliga stereokemiskt isomera former och/eller möjliga tautomera former därav, i vilken formeln
15 R1 är väte, halogen, lH-imidazol-l-yl, lägre aryl- oxi, aryloxi, aryllägre alkyloxi, lägre alkyltio, aryltio, hydroxi, merkapto, amino, lägre alkylsulfinyl, lägre alk-ylsulfonyl, cyano, lägre alkyloxikarbonyl, lägre alkyl-karbonyl eller lägre alkyl;
20 R2 och R3 är oberoende av varandra väte eller lägre alkyl, eller R2 och R3 tillsammans kan bilda en bivalent radikal med formeln -CH=CH-CH=CH-; A är en bivalent radikal med formeln
25 -CH=N-CH=CH- (a), R4 -C.H2l.-N-CnH2n- (b),
30 R5 R6 -C„H2lll-C-CnH2n- (c) eller R7 R® -CWW^-C =C-CnH2n- (d), 74 8 5373 väri nägon av väteatomerna i gruppen CmH2m, Cm.1H2(B.1) eller CnH2n kan vara ersatt av lägre alkyl eller aryl; m och n är oberoende av varandra heltal 1-4, var-vid summan av m och n är 3, 4 eller 5;
2. Förfarande enligt patentkravet 1, känne-t e c k n a t därav, att A är en bivalent radikal med 30 formeln b, väri R4 är aryl, pyridinyl, pyrimidinyl, lägre alkoxikarbonyl, aryllägre alkyl, diaryllägre alkyl eller kinolinyl; eller A är en bivalent radikal med formeln c, väri R5 är väte, aryl, arylamino, (aryl)(lägre alkyl)amino, hydroxi eller indolyl och R6 är väte, aryl, arylkarbonyl 35 eller (arylkarbonyl)lägre alkyl; eller A är en bivalent radikal med formeln d. 77 ö 5 3 7 3
3. Förfarande enligt patentkravet 2, känne-t e c k n a t därav, att R2 och R3 vardera är väte.
4. Förfarande enligt patentkravet 3, känne-t e c k n a t därav, att i den bivalenta radikalen A med 5 formeln b är m heltalet 2 eller 3 och n är 2; i radikalen A med formeln c är m heltalet 1 eller 2 och n är heltalet 2; och i radikalen A med formeln d är m heltalet 1 eller 2 och n är heltalet 2.
5. Förfarande enligt patentkravet 4, känne- 10 tecknat därav, att R1 är halogen, lägre alkoxi, aryloxi, lägre alkyltio, aryltio eller cyan.
5 R4 är aryl; tiazolyl; pyrimidinyl; kinolinyl; lägre alkylkarbonyl; lägre alkyloxikarbonyl; aryllägre alkyl; diaryllägre alkyl; fenyl som substituerats med arylkarbo-nyl; pyridinyl som eventuellt substituerats med cyan eller lägre alkyl; cyklohexyl eller cyklohexenyl, vilka vardera 10 eventuellt substituerats med upp tili tvä substituenter, vilka självständigt är cyan eller aryl; R5 är väte; lägre alkyl; aryl; hydroxi; lägre alkyl-oxi; aryloxi; lägre alkyloxi som substituerats med morfo-lin, pyrrolidin eller piperidin; amino; (lägre alkyloxi-15 karbonyl)amino; arylamino; (aryl) (lägre alkyl)amino; (aryllägre alkyl)amino; (aryllägre alkenyl)amino; (aryllägre alkenyl)(lägre alkyl)amino; eller arylkarbonyloxi; R6 är väte; aryl; lägre alkyl; (lägre alkylkarbonyl-amino)lägre alkyl; aryllägre alkyl; arylkarbonyllägre alk-20 yl; aminokarbonyl; arylkarbonyl; arylaminokarbonyl; (aryl lägre alkyl)karbonyl; lägre alkyloxikarbonyl; indolyl; eller pyridinyl; R7 och R8 är oberoende av varandra väte; lägre alkyl; aryl; aryllägre alkyl; eller pyridinyl; 25 varvid aryl är fenyl som, eventuellt substituerats med upp tili 3 substituenter, vilka självständigt är halogen, lägre alkyl, trifluormetyl, nitro, amino, lägre alkyloxi, hydroxi eller lägre alkyloxikarbonyl; tienyl; eller naftalenyl; med villkor att 30 i) dä A är en radikal med formeln c och R6 är väte, mäste R5 vara annat än väte, hydroxi eller lägre alkyl; ii) dä R2 och R3 är väte och A är en radikal med formeln b, mäste R4 vara annat än 3,3-difenylpropyl; iii) dä R2 och R3 är väte och A är en radikal med 35 formeln a, mäste R1 vara annat än halogen; l: 75 85373 iv) dä R1 är klor, R2 och R3 är väte och A är en radikal med formeln b, mäste R4 vara annat än 2-metoxife-nyl; v) dä R1 är klor och A är en bivalent radikal med 5 formeln b, mäste R4 vara annat än (dimetoxifenyl)metyl, (dimetoxifenyl)etyl, a-metylfenetyl eller (2-metylfenyl)-metyl; vi) d£ R1 är metoxi och A är en bivalent radikal med formeln b, mäste R4 vara annat än (dimetoxifenyl)etyl eller 10 (dimetoxifenyl)metyl; kännetecknat därav, att man a) alkylerar en amin med formeln II πίΓΛ (II) 15 med ett pyridazin med formeln III N-N 20 r1 %—w ,)=\ , (HD R RJ väri W betecknar en reaktiv, avgäende grupp, ifall önsk-25 värt, i ett reaktionsinert lösningsmedel, eventuellt i närvaro av en bas; b) alkylerar en pyridazinamin med formeln I-a N—N c Ri—/ V f m 2n^
30. V / N NH <I-a) R r3 med en reaktant med formeln IV 35 W-R4 (IV) 76 ö 5 6 Ί 6 ifali önskvärt, i ett reaktionsinert lösningsmedel, even-tuellt i närvaro av en bas, varvid erhälls en förening med formeln I-b 5 , /N_N^ H, 2 x \ 3 n 2n^ R rj 10 eller c) reduktivt N-alkylerar en pyridazinamin med formeln I-a med en karbony1förening med formeln 15 (1^-^)=0=0 väri föreningen (1^-^)=0=0 är en förening med formeln R4"b-H, väri en -CH2- radikal oxideras tili en karbonyl-grupp, och väri R4"b är aryllägre alkyl, diaryllägre alkyl, 20 cyklohexyl eller cyklohexenyl, i ett reaktionsinert lös ningsmedel, varvid erhälls en förening med formeln I-b; och ifall önskvärt, omvandlar de sälunda erhällna föreningarna med formeln I i terapeutiskt aktiv, giftfri syraadditionssaltform genom behandling med en lämplig sy-25 ra, eller omvänt, omvandlar syraadditionssaltet i den fria basformen med alkali; och/eller framställer stereokemiskt isomera former därav.
6. Förfarande enligt patentkravet 4, känne-tecknat därav, att R1 är halogen.
7. Förfarande enligt patentkravet 1, känne- 15 tecknat därav, att föreningen med formeln I är 3-brom-6-[4—(3-metylfenyl)-l-piperazinyl]pyridazin eller ett farmaceutiskt godtagbart syraadditionssalt därav.
8. Förfarande enligt patentkravet 1, känne-tecknat därav, att föreningen med formeln I är 20 3-klor-6-[3,6-dihydro-4-(3-metylfenyl)-1 ( 2H)-pyridinyl]py- ridazin eller ett farmaceutiskt godtagbart syradditions-salt därav.
FI851177A 1984-03-26 1985-03-25 Analogiförfarande för framställning av terapeutiskt användbara pyridaz inaminderivat FI85373C (sv)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US59344484A 1984-03-26 1984-03-26
US59344484 1984-03-26
US70277285 1985-02-15
US06/702,772 US5001125A (en) 1984-03-26 1985-02-15 Anti-virally active pyridazinamines

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FI851177A0 FI851177A0 (fi) 1985-03-25
FI851177L FI851177L (fi) 1985-09-27
FI85373B FI85373B (fi) 1991-12-31
FI85373C true FI85373C (sv) 1992-04-10

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US (3) US5001125A (sv)
EP (1) EP0156433B1 (sv)
KR (1) KR870001158B1 (sv)
AT (1) ATE61050T1 (sv)
AU (1) AU576563B2 (sv)
BG (1) BG43690A3 (sv)
CA (1) CA1238321A (sv)
CZ (1) CZ277730B6 (sv)
DE (1) DE3581819D1 (sv)
DK (1) DK166277C (sv)
ES (1) ES8606289A1 (sv)
FI (1) FI85373C (sv)
GR (1) GR850714B (sv)
HU (1) HU198010B (sv)
IL (1) IL74707A (sv)
NO (1) NO161257C (sv)
NZ (1) NZ211494A (sv)
PH (1) PH22495A (sv)
PT (1) PT80157B (sv)
RO (1) RO91197B (sv)
SU (1) SU1384198A3 (sv)
ZW (1) ZW5485A1 (sv)

Families Citing this family (74)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5001125A (en) * 1984-03-26 1991-03-19 Janssen Pharmaceutica N.V. Anti-virally active pyridazinamines
ES8802151A1 (es) * 1985-07-31 1988-04-01 Janssen Pharmaceutica Nv Un procedimiento para la preparacion de nuevos piridazinaminas.
NZ225045A (en) * 1987-07-01 1990-06-26 Janssen Pharmaceutica Nv Antiviral pharmaceutical compositions containing cyclodextrin and an antiviral agent
US4992433A (en) * 1987-11-23 1991-02-12 Janssen Pharmaceutica N.V. Novel pyridazinamine derivatives
US5106973A (en) * 1987-11-23 1992-04-21 Janssen Pharmaceutica N.V. Pyridzainamine derivatives
US5231184A (en) * 1987-11-23 1993-07-27 Janssen Pharmaceutica N.V. Pridazinamine derivatives
JPH01139578A (ja) * 1987-11-26 1989-06-01 Morishita Seiyaku Kk ３−（１ｈ−イミダゾール−１−イル）ピリダジン誘導体
US5070090A (en) * 1989-05-15 1991-12-03 Janssen Pharmaceutica N.V. Antipicorpaviral herterocyclic-substituted morpholinyl alkylphenol ethers
NZ233503A (en) * 1989-05-15 1991-06-25 Janssen Pharmaceutica Nv Substituted (thio)morpholinyl and piperazinyl alkylphenol ethers
GB8911158D0 (en) * 1989-05-16 1989-07-05 Janssen Pharmaceutica Nv Antiviral pyridazinamines
NZ233526A (en) * 1989-05-15 1991-09-25 Janssen Pharmaceutica Nv Pyridazine derivatives and their pharmaceutical compositions
JO1645B1 (en) * 1989-12-26 1991-11-27 شركة جانسين فارماسوتيكا ان. في Pyridazine compounds are antibacterial viruses
US5100893A (en) * 1990-04-18 1992-03-31 Janssen Pharmaceutica N.V. Antipicornaviral pyridazinamines
FR2668151A1 (fr) * 1990-10-23 1992-04-24 Rhone Poulenc Agrochimie Composes a groupe triazolopyridazine leurs preparations et compositions herbicides les contenant.
JPH05117150A (ja) * 1991-10-25 1993-05-14 Sanwa Kagaku Kenkyusho Co Ltd 抗ウイルス剤
JPH05255089A (ja) * 1991-12-18 1993-10-05 Sanwa Kagaku Kenkyusho Co Ltd 抗ウイルス剤
US5242924A (en) * 1992-07-02 1993-09-07 Sterling Winthrop Inc. Tetrazolyl-(phenoxy and phenoxyalkyl)-piperidinylpyridazines as antiviral agents
FR2703354B1 (fr) * 1993-03-31 1995-06-30 Lafon Labor Derives de 1, 2, 5, 6-tetrahydropyridine, leur procede de preparation et leurs applications en therapeutique.
DE69430861T2 (de) * 1993-04-07 2003-01-23 Otsuka Pharma Co Ltd N-acylierte 4-aminopiperidin derivate als aktive bestandteile von peripher gefässerweiternden wikstoffen
CA2133855A1 (en) * 1993-10-11 1995-04-12 Marco Baroni Heteroarylpiperidines, process for their preparation and pharmaceutical compositions in which they are present
FR2721513B1 (fr) * 1994-06-23 1996-09-06 Lafon Labor Utilisation de dérivés de 1,2,5,6-tétrahydropyridine pour la fabrication de médicaments à effet sédatif.
FR2721514B1 (fr) * 1994-06-23 1996-09-06 Lafon Labor Compositions thérapeutiques comprenant des 3-phényl-3-hydroxypipéridines.
US5753679A (en) * 1995-05-10 1998-05-19 Hoffmann-La Roche Inc. Benzyl-piperidine derivatives
NZ326354A (en) * 1996-01-15 1999-05-28 Janssen Pharmaceutica Nv 3-(substituted-1-piperazinyl)-6-(substituted-1,2,4-thiadiazol-5 -yl)-pyridazine derivatives and medicaments
FR2745811B1 (fr) * 1996-03-07 1998-05-22 Sanofi Sa Glutarimide disubstitue procede pour sa preparation, et son utilisation
DE69842058D1 (de) 1997-10-27 2011-01-27 Neurosearch As Heteroaryl Diazacycloalkane als cholinergische Ligande für Nikotin-Acetylcholin-Rezeptoren
US6251919B1 (en) * 1998-02-27 2001-06-26 Warner-Lambert Heterocyclic substituted aniline calcium channel blockers
JP2002543070A (ja) 1999-04-26 2002-12-17 ニューロサーチ、アクティーゼルスカブ ヘテロアリールジアザシクロアルカン類、その製造方法及びその使用方法
US6833370B1 (en) 1999-05-21 2004-12-21 Abbott Laboratories Heterocycle substituted aminoazacycles useful as central nervous system agents
AUPQ105499A0 (en) 1999-06-18 1999-07-08 Biota Scientific Management Pty Ltd Antiviral agents
WO2001058959A1 (en) * 2000-02-07 2001-08-16 Janssen Pharmaceutica N.V. Use of thrombin receptor antagonists against gliosis
AUPR213700A0 (en) * 2000-12-18 2001-01-25 Biota Scientific Management Pty Ltd Antiviral agents
US7390813B1 (en) 2001-12-21 2008-06-24 Xenon Pharmaceuticals Inc. Pyridylpiperazines and aminonicotinamides and their use as therapeutic agents
US20050119251A1 (en) * 2001-12-21 2005-06-02 Jian-Min Fu Nicotinamide derivatives and their use as therapeutic agents
BR0307429A (pt) * 2002-02-05 2004-12-28 Novo Nordisk As Composto, uso do mesmo, composição farmacêutica, e, método para o tratamento de distúrbios ou doenças relacionadas com receptor de histamina h3
US20030236259A1 (en) * 2002-02-05 2003-12-25 Rolf Hohlweg Novel aryl- and heteroarylpiperazines
MXPA04008097A (es) 2002-02-22 2004-11-26 Upjohn Co Derivados de piridilsulfona como antagonistas del receptor 5-ht.
HUP0200849A2 (hu) * 2002-03-06 2004-08-30 Sanofi-Synthelabo N-aminoacetil-2-ciano-pirrolidin-származékok, e vegyületeket tartalmazó gyógyszerkészítmények és eljárás előállításukra
JP4808616B2 (ja) 2003-07-30 2011-11-02 ゼノン・ファーマシューティカルズ・インコーポレイテッド ピリダジン誘導体および治療剤としてのその用途
CN101712653A (zh) 2003-07-30 2010-05-26 泽农医药公司 哒嗪衍生物和它们作为治疗剂的用途
US7759348B2 (en) 2003-07-30 2010-07-20 Xenon Pharmaceuticals Inc. Pyridazine derivatives and their use as therapeutic agents
US7754711B2 (en) * 2003-07-30 2010-07-13 Xenon Pharmaceuticals Inc. Pyridazine derivatives and their use as therapeutic agents
JP4864717B2 (ja) 2003-11-20 2012-02-01 ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ ポリ（ａｄｐ−リボース）ポリメラーゼインヒビターとしての７−フェニルアルキル置換２−キノリノンおよび２−キノキサリノン
SG150533A1 (en) 2003-11-20 2009-03-30 Janssen Pharmaceutica Nv 6-alkenyl and 6-phenylalkyl substituted 2-quinolinones and 2- quinoxalinones as poly(adp-ribose) polymerase inhibitors
MY142362A (en) 2004-01-29 2010-11-30 Otsuka Pharma Co Ltd Pharmaceutical composition for promoting angiogenesis
AU2005228289B2 (en) * 2004-03-31 2008-01-10 Nippon Soda Co., Ltd. Cyclic amine compound and pest control agent
BRPI0512938A (pt) 2004-06-30 2008-04-15 Janssen Pharmaceutica Nv derivados da quinazolinediona como inibidores parp
CA2569824C (en) 2004-06-30 2013-03-19 Janssen Pharmaceutica N.V. Phthalazine derivatives as parp inhibitors
WO2006003146A1 (en) 2004-06-30 2006-01-12 Janssen Pharmaceutica N.V. Quinazolinone derivatives as parp inhibitors
WO2006034338A1 (en) 2004-09-20 2006-03-30 Xenon Pharmaceuticals Inc. Heterocyclic derivatives and their use as mediators of stearoyl-coa desaturase
TW200624427A (en) * 2004-09-20 2006-07-16 Xenon Pharmaceuticals Inc Heterocyclic derivatives and their use as therapeutic agents
BRPI0515482A (pt) 2004-09-20 2008-07-22 Xenon Pharmaceuticals Inc derivados heterocìclicos e seus usos como agentes terapêuticos
BRPI0515477A (pt) * 2004-09-20 2008-07-22 Xenon Pharmaceuticals Inc derivados heterocìclicos bicìclicos e o uso dos mesmos como inibidores de estaroil-coa-desaturase (scd)
CN101083994A (zh) * 2004-09-20 2007-12-05 泽农医药公司 杂环衍生物及其用作硬脂酰CoA去饱和酶抑制剂的用途
BRPI0515488A (pt) 2004-09-20 2008-07-29 Xenon Pharmaceuticals Inc derivados de heterocìclicos e seu uso como agentes terapêuticos
US7829712B2 (en) 2004-09-20 2010-11-09 Xenon Pharmaceuticals Inc. Pyridazine derivatives for inhibiting human stearoyl-CoA-desaturase
WO2006034315A2 (en) 2004-09-20 2006-03-30 Xenon Pharmaceuticals Inc. Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-coa desaturase enzymes
CA2584422A1 (en) * 2004-10-18 2006-04-27 Eli Lilly And Company 1-(hetero)aryl-3-amino-pyrollidine derivatives for use as mglur3 receptor antagonists
BRPI0611187A2 (pt) * 2005-06-03 2010-08-24 Xenon Pharmaceuticals Inc derivados aminotiazàis como inibidores da estearoil-coa desaturase humana
CN1887875B (zh) * 2005-06-30 2011-04-06 深圳市东阳光实业发展有限公司 哒嗪胺衍生物及其用于制备小rna病毒抑制剂的用途
EP2233470B1 (en) * 2005-07-04 2011-12-07 High Point Pharmaceuticals, LLC Histamine H3 receptor antagonists
EP1910352A1 (en) * 2005-07-20 2008-04-16 Merck Frosst Canada Ltd. Heteroaromatic compounds as inhibitors of stearoyl-coenzyme a delta-9 desaturase
PL1932844T3 (pl) * 2005-10-06 2015-12-31 Nippon Soda Co Usieciowane cykliczne związki aminowe i środki do zwalczania szkodników
US8685961B2 (en) * 2006-03-29 2014-04-01 Merck Sharp & Dohme Corp. Diazepan orexin receptor antagonists
WO2007122411A1 (en) * 2006-04-26 2007-11-01 Astrazeneca Ab Diazepan-1-yl-sulfonyl derivatives for the treatment of metabolic syndrome
MX2008014766A (es) * 2006-05-29 2009-03-06 High Point Pharmaceuticals Llc 3-(1,3-benzodioxol-5-il)-6-(4-ciclopropilpiperazin-1-il)-piperazi na, sus sales y solvatos y su uso como antagonista del receptor de h3 histamina.
AU2008223793B2 (en) 2007-03-08 2012-08-23 Janssen Pharmaceutica Nv Quinolinone derivatives as PARP and TANK inhibitors
EP2014656A3 (en) * 2007-06-11 2011-08-24 High Point Pharmaceuticals, LLC New heteocyclic h3 antagonists
WO2009053373A1 (en) 2007-10-26 2009-04-30 Janssen Pharmaceutica Nv Quinolinone derivatives as parp inhibitors
CA2716088C (en) 2008-03-27 2017-03-07 Eddy Jean Edgard Freyne Quinazolinone derivatives as tubulin polymerization inhibitors
BRPI0909017A2 (pt) 2008-03-27 2020-11-10 Janssen Pharmaceutica N.V. tetra-hidrofenantridinonas e tetraidrociclopentaquinolinonas como inibidores de polimerização de tibilina e parp, seus usos, processos de preparação, combinação e composição farmacêutica que as compreende, bem como processo de preparação de uma composição farmacêutica
US20100041663A1 (en) 2008-07-18 2010-02-18 Novartis Ag Organic Compounds as Smo Inhibitors
CA2914762C (en) 2013-07-30 2021-11-23 Janssen Sciences Ireland Uc Substituted pyridine-piperazinyl analogues as rsv antiviral compounds
CN105829304B (zh) * 2013-12-20 2019-09-20 中国人民解放军军事医学科学院毒物药物研究所 N,n’取代哌啶胺类化合物、其制备方法及用途

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE485737A (sv) * 1947-11-12
US3014034A (en) * 1959-01-22 1961-12-19 Ciba Pharm Prod Inc 1, 3-diaryl, 5-amino-pyridazinones
US2985657A (en) * 1959-10-12 1961-05-23 Paul A J Janssen 1-(aroylalkyl)-4-heterocyclylpiperazines
GB1184714A (en) * 1965-12-16 1970-03-18 Science Union & Cie Di- and Tri-Phenylpropyl Piperazine Derivatives
GB1293565A (en) * 1969-05-03 1972-10-18 Aspro Nicholas Ltd Aminophthalazines and pharmaceutical compositions thereof
US4181723A (en) * 1973-08-02 1980-01-01 Sandoz Ltd. 3-Hydrazino-5,6,7,8,9,10-hexahydro-cycloocta[c]pyridazines
NL171985C (nl) * 1976-02-10 1983-06-16 Rhone Poulenc Ind Werkwijze voor het bereiden van preparaten met werking tegen schistosomiasis, de aldus verkregen gevormde preparaten en werkwijze voor het bereiden van 1,2-dithioolverbindingen.
US4104385A (en) * 1976-08-19 1978-08-01 Sterling Drug Inc. Cyclic alkylidenyl N-[6-(amino)-3-pyridazinyl]aminomethylenemalonates
IN148482B (sv) * 1977-06-03 1981-03-07 Pfizer
HU176100B (en) * 1977-10-25 1980-12-28 Gyogyszerkutato Intezet Process for preparing new 3-/1-pyrazolyl/-pyridazine derivatives
US4370328A (en) * 1977-11-03 1983-01-25 Pfizer Inc. Cardiac stimulant 1-(3- or 4-substituted piperidino)phthalazines
DE2935359A1 (de) * 1979-09-01 1981-03-26 Basf Ag, 67063 Ludwigshafen 6-imidazolyl-3-hydrazino-pyridazine
US4304775A (en) * 1979-12-13 1981-12-08 Sterling Drug Inc. 3-Hydrazino-6-(pyridinyl) pyridazines and cardiotonic use thereof
FI70411C (fi) 1980-12-29 1986-09-19 Pfizer Foerfarande foer framstaellning av nya antihypertensiva 4-amino-6,7-dimetoxi-2-piperazinokinazolin derivat
FR2511366A1 (fr) * 1981-08-11 1983-02-18 Sanofi Sa Nouveaux derives de la pyridazine, leur procede de preparation et les medicaments, actifs sur le systeme nerveux central, qui en contiennent
JPS5877866A (ja) * 1981-11-04 1983-05-11 Mitsui Toatsu Chem Inc アミノピリダジン誘導体および除草剤
GB2121140B (en) 1982-06-03 1985-12-04 Lucas Ind Plc Disc assemblies for brakes
FR2539741A1 (fr) * 1983-01-21 1984-07-27 Sanofi Sa Composes a noyau heterocyclique diazote, leur procede de preparation et les medicaments, actifs sur le systeme nerveux central, qui en contiennent
US5001125A (en) * 1984-03-26 1991-03-19 Janssen Pharmaceutica N.V. Anti-virally active pyridazinamines
US4661493A (en) * 1985-03-29 1987-04-28 Pfizer Inc. Tioconazole and related compounds for control of Herpes simplex virus
NZ225045A (en) * 1987-07-01 1990-06-26 Janssen Pharmaceutica Nv Antiviral pharmaceutical compositions containing cyclodextrin and an antiviral agent
US4992433A (en) * 1987-11-23 1991-02-12 Janssen Pharmaceutica N.V. Novel pyridazinamine derivatives
GB8911158D0 (en) * 1989-05-16 1989-07-05 Janssen Pharmaceutica Nv Antiviral pyridazinamines

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BG43690A3 (en) 1988-07-15
ES541521A0 (es) 1986-04-16
KR850006401A (ko) 1985-10-05
FI851177L (fi) 1985-09-27
NO851167L (no) 1985-09-27
US5157035A (en) 1992-10-20
AU576563B2 (en) 1988-09-01
NZ211494A (en) 1988-05-30
HUT37614A (en) 1986-01-23
DK134185D0 (da) 1985-03-25
IL74707A (en) 1988-05-31
RO91197B (ro) 1987-07-01
EP0156433A3 (en) 1986-07-23
KR870001158B1 (ko) 1987-06-13
NO161257C (no) 1989-07-26
HU198010B (en) 1989-07-28
DK134185A (da) 1985-09-27
US5001125A (en) 1991-03-19
DK166277B (da) 1993-03-29
FI851177A0 (fi) 1985-03-25
IL74707A0 (en) 1985-06-30
CA1238321A (en) 1988-06-21
ES8606289A1 (es) 1986-04-16
PT80157A (en) 1985-04-01
ATE61050T1 (de) 1991-03-15
AU4034885A (en) 1985-10-03
CS195285A3 (en) 1992-11-18
CZ277730B6 (en) 1993-04-14
SU1384198A3 (ru) 1988-03-23
US5292738A (en) 1994-03-08
FI85373B (fi) 1991-12-31
RO91197A (ro) 1987-06-30
DE3581819D1 (de) 1991-04-04
GR850714B (sv) 1985-06-14
NO161257B (no) 1989-04-17
EP0156433B1 (en) 1991-02-27
ZW5485A1 (en) 1986-10-22
DK166277C (da) 1993-08-30
PT80157B (en) 1987-03-20
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PH22495A (en) 1988-09-12

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